US4244957A
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2-Imino-imidazolidine derivatives
Assignee: Hoffmann La Roche Inc
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Filing: 1978-11-06
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Granted: 1981-01-13
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Expires: 1998-11-06
Abstract
Abstract 2-Imino-imidazolidine derivatives of the formula <IMAGE> wherein R1, R2, R3 and R4 are as hereinafter set forth, and pharmaceutically acceptable acid addition salts thereof, are described. The 2-imino-imidazolidine derivatives are useful in the treatment of hypertension.
Inventors
- 👤 Henri Ramuz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 06:44
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; A; A61; A61P; A61P29/00; A61P9/00; A61P9/04; A61P9/12; C07C; C07C335/00; C07C335/40; C07D233/00; C07D233/04; C07D233/28; C07D233/44; C07D233/50; C07D491/00; C07D491/02; C07D491/04
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
108 words
A compound of the formula ##STR17## wherein R 1 , R 2 and R 3 , independently, are hydrogen, alkyl, alkoxy, alkylthio, halogen, trifluoromethyl, cyano or hydroxy and R 4 is [5-hydroxy-4-hydroxymethyl)-6-methyl-3-pyridyl]-methyl or an aromatic 6-membered heterocyclic residue selected from the group consisting of pyridyl, pyrimidinyl and pyrazinyl, which is bonded via a --CH(R 5 )-- group and is optionally substituted by alkyl, alkoxy or the group --COOR, wherein R 5 is hydrogen, methyl, ethyl or n-propyl and R is hydrogen or alkyl, and wherein above, each occurrence, the alkyl, alkoxy and alkylthio groups, independently, are of 1-6 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
108 words
A compound of the formula ##STR17## wherein R 1 , R 2 and R 3 , independently, are hydrogen, alkyl, alkoxy, alkylthio, halogen, trifluoromethyl, cyano or hydroxy and R 4 is [5-hydroxy-4-hydroxymethyl)-6-methyl-3-pyridyl]-methyl or an aromatic 6-membered heterocyclic residue selected from the group consisting of pyridyl, pyrimidinyl and pyrazinyl, which is bonded via a --CH(R 5 )-- group and is optionally substituted by alkyl, alkoxy or the group --COOR, wherein R 5 is hydrogen, methyl, ethyl or n-propyl and R is hydrogen or alkyl, and wherein above, each occurrence, the alkyl, alkoxy and alkylthio groups, independently, are of 1-6 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
86 words
A compound in accordance with claim 1, wherein R 1 , R 2 and R 3 , independently, are hydrogen, alkyl, alkoxy, alkylthio, halogen, trifluoromethyl, cyano or hydroxy and R 4 is [5-hydroxymethyl)-6-methyl-3-pyridyl]-methyl or pyridyl, which is bonded via a --CH(R 5 )-- group and is optionally substituted by alkyl or the group --COOR, wherein R 5 is hydrogen, methyl, ethyl or n-propyl and R is hydrogen or alkyl, and wherein above, each occurrence, the alkyl, alkoxy and alkylthio groups, independently, are of 1-6 carbon atoms.
Claim 4
Dependent Claim
14 words
A compound in accordance with claim 1 or 2, wherein R 3 is hydrogen.
Claim 5
Dependent Claim
24 words
A compound in accordance with claim 1, 2, or 3, wherein R 1 and R 2 are located in the 2,6-position of the phenyl-ring.
Claim 6
Dependent Claim
16 words
A compound in accordance with claim 4, wherein R 1 and R 2 are the same.
Claim 7
Dependent Claim
15 words
A compound in accordance with claim 5, wherein R 1 and R 2 are halogen.
Claim 8
Dependent Claim
15 words
A compound in accordance with claim 6, wherein R 1 and R 2 are chlorine.
Claim 9
Dependent Claim
42 words
A compound in accordance with claim 1 or 2, wherein R 3 is hydrogen, R 1 and R 2 are halogen, in the 2,6-position, R 4 is pyridyl bonded via a --CH(R 5 )-- group and R 5 is hydrogen or methyl.
Claim 10
Dependent Claim
8 words
A compound in accordance with claim 2, 2-{[<2-[(2,6-dichlorophenyl)-imino]-1-imidazolidinyl>oxy]methyl}pyridine.
Claim 11
Dependent Claim
8 words
A compound in accordance with claim 2, 3-{[<2-[(2,6-dichlorophenyl)-imino]-1-imidazolidinyl>oxy]methyl}pyridine.
Claim 12
Dependent Claim
8 words
A compound in accordance with claim 2, 2-{[<2-[(2,6-dichloro-4-fluorophenyl)imino]-1-imidazolidinyl>oxy]methyl}pyridine.
Claim 13
Dependent Claim
8 words
A compound in accordance with claim 2, 5-{[<2-[(2,6-dichlorophenyl)imino]-1-imidazolidinyl>oxy]methyl}-3-hydroxy-2-methyl-4-pyridinemethanol.
Claim 14
Dependent Claim
128 words
A composition for the treatment of hypertension which comprises a hypotensively effective amount of a compound of the formula ##STR18## wherein R 1 , R 2 and R 3 , independently, are hydrogen, alkyl, alkoxy, alkylthio, halogen, trifluoromethyl, cyano or hydroxy and R 4 is [5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridiyl]-methyl or an aromatic 6-membered heterocyclic residue selected from the group consisting of pyridyl, pyrimidinyl and pyrazinyl, which is bonded via a --CH(R 5 )-- group and is optionally substituted by alkyl, alkoxy or the group --COOR, wherein R 5 is hydrogen, methyl, ethyl or n-propyl and R is hydrogen or alkyl, and wherein above, each occurrence, the alkyl, alkoxy and alkylthio groups, independently, are of 1-6 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof and an inert pharmaceutical carrier material.
Claim 15
Dependent Claim
128 words
A composition for the treatment of hypertension which comprises a hypotensively effective amount of a compound of the formula ##STR18## wherein R 1 , R 2 and R 3 , independently, are hydrogen, alkyl, alkoxy, alkylthio, halogen, trifluoromethyl, cyano or hydroxy and R 4 is [5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridiyl]-methyl or an aromatic 6-membered heterocyclic residue selected from the group consisting of pyridyl, pyrimidinyl and pyrazinyl, which is bonded via a --CH(R 5 )-- group and is optionally substituted by alkyl, alkoxy or the group --COOR, wherein R 5 is hydrogen, methyl, ethyl or n-propyl and R is hydrogen or alkyl, and wherein above, each occurrence, the alkyl, alkoxy and alkylthio groups, independently, are of 1-6 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof and an inert pharmaceutical carrier material.
Claim 16
Independent Claim
127 words
A method of treating hypertension which comprises administering to a warm-blooded animal requiring such treatment a hypotensively effective amount of compound of the formula ##STR19## wherein R 1 , R 2 and R 3 , independently, are hydrogen, alkyl, alkoxy, alkylthio, halogen, trifluoromethyl, cyano or hydroxy and R 4 is [5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridyl]-methyl or an aromatic 6-membered heterocyclic residue selected from the group consisting of pyridyl, pyrimidinyl and pyrazinyl, which is bonded via a --CH(R 5 )-- group and is optionally substituted by alkyl, alkoxy or the group --COOR, wherein R 5 is hydrogen, methyl, ethyl or n-propyl and R is hydrogen or alkyl, and wherein above, each occurrence, the alkyl, alkoxy and alkylthio groups, independently, are of 1-6 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.
Claim 17
Independent Claim
127 words
A method of treating hypertension which comprises administering to a warm-blooded animal requiring such treatment a hypotensively effective amount of compound of the formula ##STR19## wherein R 1 , R 2 and R 3 , independently, are hydrogen, alkyl, alkoxy, alkylthio, halogen, trifluoromethyl, cyano or hydroxy and R 4 is [5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridyl]-methyl or an aromatic 6-membered heterocyclic residue selected from the group consisting of pyridyl, pyrimidinyl and pyrazinyl, which is bonded via a --CH(R 5 )-- group and is optionally substituted by alkyl, alkoxy or the group --COOR, wherein R 5 is hydrogen, methyl, ethyl or n-propyl and R is hydrogen or alkyl, and wherein above, each occurrence, the alkyl, alkoxy and alkylthio groups, independently, are of 1-6 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-01-13 | 1984-07-14 | 1985-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-01-13 | 1988-07-14 | 1989-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-01-13 | 1992-07-14 | 1993-01-13 | $7700.00 | Window Closed / Lapsed |